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- Title
One-Pot Synthesis of 3-Substituted 3,4-Dihydro-1,2,3-benzotriazine Derivatives Based on the Reaction of o-Bromobenzyl Azides with Butyllithium.
- Authors
Kobayashi, Kazuhiro; Chikazawa, Yuuki
- Abstract
An efficient one-pot procedure for the preparation of 3-substituted 3,4-dihydro-1,2,3-benzotriazines 2, 3, and 4 from o-bromobenzyl azides 1 is described. The reaction of these azides with BuLi in THF at −78° generates o-lithiobenzyl azides via the Br/Li exchange. These lithium compounds immediately undergo intramolecular cyclization to give the corresponding (dihydro-1,2,3-benzotriazinyl)lithium intermediates, which are trapped with a variety of acylating agents or BnBr at N(3) exclusively to provide the desired products in moderate to good yields.
- Subjects
AZIDES; BUTYLLITHIUM; NITROGEN compounds; CHEMICAL synthesis; CHEMICAL bonds; CHEMICAL structure
- Publication
Helvetica Chimica Acta, 2016, Vol 99, Issue 1, p33
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201500234